I have type II diabetes and have to use penile injection theropy, we use my condition for her push to fuck other men, it has been a turn on for both of use, she is getting into letting me have a cream pie, she loves to kiss me after a blow job, we started with having sex after to allowing her over nights!
I Have ED and She is a Hot Wife/GF
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If you want, the ED can be a reason for you to be more of a sissy, too. You can approach it with the idea that the injections are expensive and painful, so you want to explore "other" sexual outlets - and she can help you. Creampies are a good start. She can have to present during or at the end of her pleasurings so you can clean up. That can naturally lead to you getting the bf ready for her. Later you can move to having her fuck you with a strapon and introduce crossdressing and feminization.
But these are all options open to you both. Do what you are both comfortable doing and only push the envelope when you are ready. I'm just pointing out you have a ready-made reason if she wonders why you might be thinking this way.
We have talked about her using a strap on and fucking me - but that is a ways off, sje is not into male on male sex at all, a 3some is far off yet as well, she currently date fucks her 2 guys either at their place or hers, sometimes she has come over when she is finished.
what a shame 
sucks to be you cuckster!
sucks to be you cuckster!
Well we enjoy her date fucks, she likes to come over after, but doesn't happen all the time, I could be an ass and say they all have to come over after, but I'm not cause I live her being fucked!
I think you should read lots of hot wife and cuckold stories on Literotica Free Stories, and print off the ones you enjoy the most, so as to "put ideas into her head for the future". When she is at the top of her game, she will gain the confidence to "spread her wings" into new areas of eroticism which formerly were outside her imagination.